ChemFOnt: Showing chemical card for Chrysosplenol (CFc000282252)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:26 UTC

Chemfont ID

CFc000282252

Molecule Identification

Common Name

Chrysosplenol

Definition

Chrysosplenol, also known as quercetagetin 3,7,3'-trimethyl ether or 4',5,6-trihydroxy-3,3',7-trimethoxyflavone, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, chrysosplenol is considered to be a flavonoid lipid molecule. Chrysosplenol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Chrysosplenol can be found in german camomile, which makes chrysosplenol a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4',5,6-Trihydroxy-3,3',7-trimethoxyflavone	ChEBI
Quercetagetin 3,7,3'-trimethyl ether	ChEBI

Chemical Formula

C₁₈H₁₆O₈

Average Molecular Weight

360.3148

Monoisotopic Molecular Weight

360.084517488

IUPAC Name

5,6-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxy-4H-chromen-4-one

Traditional Name

chrysosplenol C

CAS Registry Number

23370-16-3

SMILES

COC1=C(O)C=CC(=C1)C1=C(OC)C(=O)C2=C(O)C(O)=C(OC)C=C2O1

InChI Identifier

InChI=1S/C18H16O8/c1-23-10-6-8(4-5-9(10)19)17-18(25-3)16(22)13-11(26-17)7-12(24-2)14(20)15(13)21/h4-7,19-21H,1-3H3

InChI Key

QQBSPLCHDUCBNM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

3p-methoxyflavonoid-skeleton
3-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
6-hydroxyflavonoid
Flavone
Hydroxyflavonoid
3-methoxychromone
Chromone
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Pyranone
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyran
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trihydroxyflavone (CHEBI:3690 )
trimethoxyflavone (CHEBI:3690 )
flavonols (C10031 )
Flavones and Flavonols (C10031 )
Flavones and Flavonols (LMPK12112982 )
a small molecule (CPD-10520 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302736)

Food

Herb and spice

Herb

German camomile (FooDB: FOOD00107)

Not Available

EC 1.1.1.21 (aldehyde reductase) inhibitor (HMDB: HMDB0302736)

Anti-inflammatory (HMDB: HMDB0302736)
Anti spasmodic (HMDB: HMDB0302736)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.07 g/L	ALOGPS
logP	2.9	ALOGPS
logP	2.26	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.44	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92.56 m³·mol⁻¹	ChemAxon
Polarizability	35.61 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon